Benzene → 2-Oxazolidinone

Participants

Role	Name	HCID	Charge
Reactant	Benzene	HCID 241	—
Reactant	Formaldehyde	HCID 712	—
Reactant	Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-	HCID 18462	—
Reactant	N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine	HCID 66733684	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-Oxazolidinone	HCID 73949	—
Product	tert-Butyl 5-oxooxazolidine-3-carboxylate	HCID 20628126	—

Reaction Steps

A mixture of the iodo amino acid 23 (0.86 mmol), camphorsulfonic acid (0.17 mmol), paraformaldehyde (1.29 mmol) and benzene (10 mL) was refluxed for 2 h. The mixture was diluted with ethyl acetate and was washed with 5% aqueous sodium bicarbonate solution. The organic phase was dried with anhydrous sodium sulfate, filtered and purified by silica gel column chromatography using 40% EtOAc/Hexane mixture as eluent to obtain pure oxazolidinone product 24 (N-(tert-butoxycarbonyl)-1,3-oxazolidin-5-one derivative) as an oil in 35% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08742139B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-046f4b8558d14af5896e4b4cb541b9be
Source note	uspto-grants-2014_06